


A Winning Deal

by pushkin666



Category: Supernatural
Genre: Alternate Universe, BDSM, Dark Dean, Future Fic, John Winchester is a bastard, M/M
Language: English
Status: Completed
Published: 2010-02-13
Updated: 2010-02-13
Packaged: 2017-10-07 05:42:05
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,114
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/61978
Author URL: https://archiveofourown.org/users/pushkin666/pseuds/pushkin666
Summary: <blockquote class="userstuff">
              <p>AU futurefic. Dean and Sam are not related in this. John Winchester owes mobster Dean a great deal in gambling debts. Sam agrees to pay off his father's debt by becoming Dean's 'Companion' for a year.</p>
            </blockquote>





	A Winning Deal

Dean Roberts took a mouthful of whisky, slowly savouring the taste and aroma. He knew there were a galaxy of drinks to taste out there but he was a simple man in many respects and he liked things to be straightforward and honest - like the people he ripped off. He smiled. Well, ripped off wasn't quite true. As far as he was concerned he was providing entertainment. If people chose to spend their credits in his casinos and brothels then that was their prerogative. Far be it for him to tell them what to do with their lives, their hard earned wages. He was quite happy to get rich from their stupidity. And if they ever argued with him or his men, protested too much, or became a nuisance well, there were always ways to quiet a person down. His reputation was such that few people tried to cross him, but there were always a few that didn't learn.

He put the glass down and glanced at his watch checking to see what time it was. Not much longer now. His last meeting of the day was due shortly. He ran his fingers over the dial. The watch was a beautiful item of jewellery, the heavy metal gleaming dully against his skin. It was a 20th century timepiece received as a birthday present from one of his associates; somebody trying to curry favour. He didn't mind, he knew what the gift was worth and at least they'd taken the time to think about what he might like. So many people these days were happy to have timepieces implanted in their bodies, along with other fripperies. Not him though. No matter what the corporations said in their advertising he knew it was just propaganda; the implants were traceable. He had enough monies in a couple of the corporations himself to know full well what the implants could and were used for.

He sighed and looked out of his office window. From here you could see out to the bay where the remnants of the Kentowy Bridge, that miraculous piece of engineering, still showed above the waterline. Even now, fifty years after the storm, it was still standing. The view from this level was stunning, a very useful distraction when meeting with people - drawing their attention away from him and what he might be suggesting.

The Roberts Building stood fifteen levels high. This floor was solely made up of the executive offices and meeting rooms. Above this floor were three more, the one immediately above for his personal staff and the other two for his own use. Other associates, including casino and security staff, lived on the lower floors. There you could find that most prestigious of all of his establishments - The Roadhouse. A place to while away your hours, spend all of your money, and indulge in vices that you didn't even realise you had. He laughed. It was a good thing that he wasn't the person responsible for coming up with their marketing slogans.

He took another mouthful of the whisky. This visit was likely to be unpleasant but he was tired of listening to John Winchester's excuses. The man owed him a great deal in gambling debts and as far as he was concerned it was time the monies were paid. So a week ago he ordered his men to take John's youngest son, the six year old Michael into 'safe keeping' as an assurance that the debts would be paid. He knew that Winchester had the money, but he also knew that he wasn't going to pay up without an incentive. So here it was. He'd seen the child when it was first brought in and handed over to one of his staff to look after but other than that he'd kept well clear of it. He had no desire to interact with a child that he may end up having to harm or kill to make his point. He would do it, had done it before. It didn't particularly bother him. Threats to children were always an assured way of making people pay up and if he needed to use them as an example, then he would.

It wasn't helped, of course, by the fact that John had taken on the occasional enforcement job for him in the past. Perhaps that's why up until a week ago John thought he was safe from any repercussions for his actions. Dean snorted. The man was plainly stupid, and a drunk to boot, which is why he stopped using him. What was the point of somebody who couldn't even see straight enough to fire a gun? So a week ago the child was taken and John was informed, quietly, what was expected of him and when he should attend upon Dean's offices. No doubt a long week for Winchester but hopefully it would help him come around to Dean's way of thinking. He rubbed the back of his neck. His shoulders and neck ached. He was currently without a Companion so there was no chance of a massage unless he took a trip downstairs.

It was a pain not having a Companion, but the untimely and unforeseen death of his previous one was making it difficult to find a new one. It was ridiculous that a man of his position did not have a Companion. Companions were the norm in their society and talk was already circulating as to his Companionless status. His assistant had quietly approached a number of the unattached freelance Companions only to be turned down. His hand tightened around the glass. Out of all the Companions he'd contracted over the years Stuart was the only one who'd died, killed by one of Dean's enemies. Undeterred, his assistant moved on to the Companions Guild. They couldn't refuse to supply a Companion but the terms and demands they were asking of him were patently ridiculous. They'd doubled the normal fee and were demanding twenty-four hour security. There was no way he was going to provide a bodyguard for his Companion. He found it offensive that they would even suggest it. Beside if the Companion didn't feel safe going outside there was no reason they had to. The only time they would need to go out would be at his side and then there was always security. If a contract wasn't agreed soon he'd be more than happy to release the dossier he held on two of the Senior Guildsmen. Even in these decadent times Guildsmen were supposed to be squeaky clean. The fact that two of them enjoyed the delights of underage children was not something that was in the public domain, but Dean would be more than happy to release that information, along with images and even sworn testimonies if need be.

He nodded to the ever-present shadow who sat in the corner of the room. Bodyguards were essential. There were enough people out there willing to try and take him out, take over his city. He had a team of bodyguards, but Adam was the one that was always close by, hell he was one of the few people that had the passwords to Dean's quarters, knew how to access Dean's private lift. Not only did he have his own quarters on the floor below Dean's, he also had rooms of his own in Dean's apartment for when he was needed. He answered solely to Dean, had done so since Dean rescued him from one of his competitor's illegal pleasure houses - one of those specialising in younger whores. Dean was determined to not allow any pleasure houses in this city except his own, and the revenue generated from them went straight into his pockets. He'd known as soon as he saw the young man that there was something there that could be cultivated, binding him to Dean. Adam was one of the few people Dean trusted. He would always put Dean's interest over and above anything else, as he'd shown with Stuart.

He took the seat at his desk and read through a few reports before letting his assistant know that Winchester should be buzzed through. The delay was intentional. Psychologically it put the man at a disadvantage, gave him time to think about what might happen if he didn't agree to Dean's demands, if he would see his son again.

Adam took up position behind him. Dean watched as two of his guards entered, followed by John Winchester and his oldest son Samuel . Oh yes. Very nice. He swallowed as he took in the young man, letting his eyes trail up the long body, taking in the muscles that clearly showed under the tight shirt. It was a shame about the loose trousers; he'd like to see the boy's ass in something a little more fitted. His gaze carried on up until he reached the face; a strong face, with thick shaggy hair and blue-green eyes.

He forced his mind back to the details laid out in the dossier he held on John Winchester. The twenty-two year old was the son of Winchester's first marriage. His mother dying in a fire when the boy was six months old, suspicion falling on Winchester, but nothing was ever proved. Winchester'd married again eight years ago, and the son Michael was the progeny of that marriage. From what he read it was clear there was some animosity between the father and son; the boy leaving for university when most children stayed at home. He was surprised, therefore, to see him here, wondered what the boy would bring to the table. He smiled to himself.

The two Winchesters sat and his men took up their place behind them. He knew they weren't carrying weapons, everybody was searched before being brought before him, but that still didn't mean they wouldn't try something.

"John." He smiled at the younger man. "Sam, if I'm right." Sam seemed surprised that Dean knew who he was and gave a quick nod.

"I want to see my son," John said.

" Fine, pay your debts. You owe me ..." he looked down at the report, "Fifty thousand credits." He smiled at the boy's shocked gasp. "You didn't know? " he asked, looking at Sam. "I've given your father over a year now to pay the money back and now ..." He leaned back in his seat, "Now he's out of time." He turned his attention back to John. Winchester looked crap. He'd clearly been drinking again, he was unshaven and his eyes were bloodshot. Dean pushed the report over to them. "If you look at this it clearly shows that you can afford to pay me back John. I fail to see why you haven't. Did you really think I would let it go simply because you once worked for me? You owe me money, and you should know I always collect."

He sat back and stared at them. Watched as Sam perused the report, his jaw tightening as he read the evidence in front of him.

John said nothing but Sam pushed the report back to him. "He doesn't have the money.," he said.

"The report says he does." Dean replied.

"No. What your report doesn't tell you is that the majority of that money is mine. He can't touch it without my agreement. Its money that came from the trusts set up by my mother's family for me. It's there to pay for me to go through university so I'm not reliant upon my father. For some reason," his voice turned scathing as he looked over at John. "My mother's family didn't believe that my father would be able to provide for me. So it's not his. If you investigate it more fully you'll see that he can only pay about half of what he owes you. Can't you come up with some sort of payment plan?" His eyes pleaded with Dean. Pretty eyes. Dean thought. He'd like to tie Sam up and have him plead with him to be released, make him turn those puppy-dog eyes on Dean and see just what reaction they'd invoke. He didn't think Sam would like the result.

Dean looked over at John. The man said nothing, his head down. "Are you incapable of speaking for yourself, John?" he asked. "Do you allow your son to be your advocate? God you're pathetic."

John lifted his head and stared at him. Dean took in the anguished expression with satisfaction. "Please Dean. I can't afford it. You know that."

Dean leant in. "If you can't afford to pay your gambling debts then you shouldn't gamble, should you." he said softly. He pushed his chair back and stood up. "I've had enough of this." he told them. "I want the money, Winchester. If you don't get it to me by tomorrow then your son dies."

"No, you can't!" Adam moved in front of him as Sam surged to his feet, and Sam's guard pulled him back.

"I can do whatever the hell I like." Dean told him. "You Winchesters," he said scornfully. "You've had a week to sort this out and what do I get? Whining about the fact that you can't afford it. The money is there. I don't care whose it is. I want the fifty thousand credits tomorrow. If not the child dies, it's as simple as that."

"Sam," John looked towards his eldest son. "Sam, please!"

Dean watched with interest as Sam swallowed, sat back down and dropped his head in his hands. He shook his head. "Dad, I can't. Please don't ask this of me."

John put his hand on Sam's arm. "He's your brother. You should do whatever you can to save him. That's what families do, they help each other."

Sam raised his head and glared at his father, obviously not impressed with the sentiment. "I can't believe you're asking this of me – you know that money's the only thing that will get me through school. Please Dad…" Dean watched as they stared at each other. Finally, Sam reluctantly turned his gaze to Dean

"I have a proposition for you." he said shakily. He was pale. Dean watched as a bead of sweat ran down his face, followed the track of it down Sam's neck until it disappeared.

"Yes?" He prompted, and then casually turned to Adam and passed him his empty glass. "Adam, would you mind?" A moment later a full glass of whisky was set in front of him. He ran his finger over the rim of the glass before smiling up at the boy, who looked like he was struggling with his decision. "So," he asked. "What do you think you can possibly offer me that might change my mind?"

He watched in bemusement as Sam reached over and picked up the glass. He took a large mouthful before putting it back down in front of Dean. "You don't have a Companion at present," he finally got out.

Dean shifted in his seat. "So?"

"Word out on the streets is that you're having problems contracting a new Companion due to the way your previous Companion left you."

Dean smiled. What an interesting way to put it. He wondered where this was going. Mentioning his Companionless status was a sure fire way to piss him off. He wondered whether the boy realised that or whether he was at the point where he simply didn't care. Sam looked down at his hands, his hair falling into his face. Dean swallowed. What wouldn't he like to do to that hair, run his hands through it, and hold the younger man down as he fucked his mouth? Almost as though Sam could hear his thoughts he glanced up at Dean and smiled a soft hesitant smile. He pushed his hair back and sat up straight.

"What I'm proposing ..." he said softly. "Is that I contract with you as your Companion for a year. The Contract wipes out the debt owed by my father."

He began to count off points on his fingers. "I'm intelligent. I started and finished University four years early and I'm going to be working on my doctorate next. I'm fit; I work out every day and know how to use a gun. I'm good company and ..."

"What are you like in bed?" Dean interrupted him. "Because, let's be honest, that's quite important don't you think? Have you ever had sex with a man?" He watched in amusement as Sam flushed bright red before he gave Dean a quick nod.

"I've had no complaints so far," he replied, looking anywhere but at Dean. It was quite endearing, actually, but shyness was something that Dean wouldn't want all of the time. Still, it was an interesting offer, and he didn't think he would have any problems in taking the boy on as his Companion. He wasn't going to write off the debt that easily though. He looked over at the elder Winchester, caught his gaze and held it until the man lowered his eyes in shame.

He took a sip of the whisky and stared at Sam. "Alright," he said, watching the way Sam's shoulders jumped, although he still looked tense. "I'm quite agreeable to taking you on as my Companion, however, I still want half of the money. The contract won't wipe out the full debt. You pay me twenty five thousand credits, and they'd better be yours John, not your son's and Sam here signs the contract tonight. You do that and I'll let you have Michael back. The debt will be wiped clean."

Sam looked over at John. "Dad?" he said, "It's a good offer, Dad. You know you can afford it." The two of them stared at each other and then John nodded once and turned towards Dean.

"Alright, Roberts,." he growled. "We have a deal. Now I want to see my son."

Dean's hand twitched towards his drawer. He really just wanted to take his gun out and shoot him. John Winchester was scum. Nothing more. Dean shook his head. The man was unbelievable; first of all to put himself in this position, and then to prostitute his own son to pay off his debts. He didn't think there was any way that Sam had come up with this idea himself. It had John Winchester written all over it. Not that he cared. It was an ideal solution, he received half of the money owed to him and he didn't have to deal with the Guild. He could keep the dossier for another time and in contracting Sam Winchester as his Companion he would have the opportunity to see what the boy was made of, what it would take to break him.

He nodded to the guards. "Take him to see his son. I'll get the contract settled with Sam. You'd better be back here tomorrow Winchester, thirteen hundred hours prompt with the twenty five thousand credits or this deal is over. Understood?"

John nodded and looked over at Sam. "Sam?" he said.

"He stays here for the moment." Dean grinned lasciviously at Sam and pushed back his chair. Undid his trousers. "He's going to prove to me that he knows exactly what he's doing, knows what I expect from a Companion."

He spread his legs and took his cock out. "Sam," he said although he kept his eyes fixed on John. "I want you over here on your knees sucking my cock. You can stay and watch if you like, John." He gave John a feral smile, enjoying the sick expression that appeared on the man's face.

"God. Sam ..." John stretched out a tentative hand towards his eldest son.

Sam ignored it, giving him a tight smile instead. "Get out of here, Dad. I don't want you to see this."

Dean ran his hand over his erect cock as he watched them. Winchester turned away abruptly and left the room, the two guards with him. Adam remained at Dean's back. Dean looked over at Sam and raised an eyebrow. "Well," he said. "What are you waiting for?"

Sam stood and walked around the desk., He dropped to his knees in front of Dean, his eyes holding Dean's the whole time. Dean removed his hand from his cock and spread his legs a little more to allow Sam to move closer to him. He tensed as soft breath wafted over the head of his cock and then Sam's hand was wrapping around him, his tongue tentatively licking the head of Dean's cock. He gasped as the head was sucked into Sam's warm mouth. He stared down at Sam. All that hair was blocking his view of the boy's face; that wasn't acceptable. He put his hands in Sam's hair, pushing it back. Sam's mouth was stretched over his cock, his lips slick with saliva and pre-come.

"That's it," he said. "Take it all. I want to see you take it all."

Sam glanced up at him and slowly began to slide his mouth further down until his nose was pressed against Dean's groin. Dean groaned as the whole of his cock was encased in the warm wet mouth, the head touching the back of Sam's throat.

"Oh shit, that's good." he said, stroking his hand through Sam's hair before grasping the back of his head to hold him steady so Sam couldn't move back.

He felt the tensing of Sam's body as he tried not to panic, tried not to pull back away from Dean. Sam's hands gripped Dean's thighs tightly, holding on to him.

Dean pulled back slightly and then pushed in, enjoying the feel of Sam's throat stuttering around him. He relaxed his hands; letting the boy take up his own motion as he huffed out a breath through his nose in quiet relief. Closing his eyes he relaxed his head back, enjoying the feeling as Sam worked his cock, his mouth sliding up and down, his soft tongue swirling around his flesh, licking the thick vein underneath. He groaned softly as Sam swallowed around him, tensing up. He knew he was going to come soon. He sat up and grasped Sam's head again firmly.

"Hold still," he told him in a tight voice. "I'll finish this. You just take what I'm going to give you." Sam swallowed around him again but did as instructed, simply holding his mouth around Dean's cock as Dean started to fuck his face, pushing his cock harder into Sam's lush mouth. His eyes looked up in panic as Dean raped his mouth. Dean said nothing, simply taking a firmer hold. He could feel his balls drawing up, knew he was about to come. "Swallow it," he growled. "I want to see you swallow every last bit. Understand?"

Sam gave a small nod, his eyes wide as he stared at Dean. Dean quickened his thrusts, watching his cock slide in and out of the Sam's mouth, and then he was coming, filling Sam's mouth, feeling him swallowing around him. He shuddered to a stop and let go of Sam's head, running the back of his hand over Sam's cheek.

Sam looked debauched and distraught, his lips swollen and bruised, eyes wide and bright with unshed tears. Dean pulled himself out of Sam's mouth and wiped his cock off before tucking himself away. He looked down at the boy. Sam needed to know what Dean would expect of him.

Dean liked his Companions to be younger than himself, liked them to have a spark of personality but when it came to sex Dean was in charge. He liked to dominate his Companions in bed; liked to mark and bruise them, make them come as and when he demanded. Liked to hurt them.

"Very good." he said in a soft voice. "If you do everything like that I'll be more than satisfied with you."

He brushed his thumb over Sam's bruised lip. "What a pretty thing you are," he told him. "I'm going to enjoy finding out what makes you tick and when I do, I'm going to take you apart, piece by piece, and maybe..." he bent down and lowered his voice as though to reveal a secret. "If you're really lucky, I might put you back together again."

He relished the look of distress in the boy's eyes.

He passed the glass of whisky to Sam. "Here," he told him. "Finish that off and then get back into your seat. We need to get the contract signed, don't we, Sammy?"

Sam stood and wiped his mouth. "It's Sam." he said, his voice soft and hoarse.

Dean grinned.

"No." He told him. "It's whatever I want it to be."


End file.
